Acetic Anhydride → HCID 178472001, compound

HRID 561120

Reaction equation

HRID 561120 reaction equation
[F:1][C:2]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[CH:12][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[CH3:19]C(OC(C)=O)=O.C(OCC)(OCC)OCC.[NH2:36][C:37]([CH3:42])([CH3:41])[CH2:38][CH2:39][OH:40]>C1(C)C=CC=CC=1>[F:1][C:2]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[CH:12][C:3]=1[C:4]([C:6](=[CH:19][NH:36][C:37]([CH3:42])([CH3:41])[CH2:38][CH2:39][OH:40])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoateHCID 6410003-Amino-3-methylbutan-1-ol

Product 1

HCID 178472001HCID 178472001, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of ethyl (2,3,4,5-tetrafluorobenzoyl)acetate (3.73 g, 14.1 mmol), Ac2O (8.50 mL, 85.7 mmol) and triethyl orthoformate (4.70 mL, 28.2 mmol) was heated at 120° C. for 3 h. The mixture was concentrated in vacuo and dried under high vacuum. To the mixture of the residue in anhydrous toluene (50 mL) was added 3-amino-3-methyl-1-butanol (1.45 g, 14.1 mmol) in anhydrous toluene (20 mL) very slowly at 0° C. and stirred at room temperature for 2 h. The solvent was removed by evaporation. Flash chromatography (EtOAc:Hexane=1:1) of the residue gave ethyl 2-(2,3,4,5-tetrafluorobenzoyl)-3-[(1-hydroxy-3-methylbutane-3-yl)amino]acrylate as a colorless solid (3.91 g, 73%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customdried under high vacuum
  3. additionTo the mixture of the residue in anhydrous toluene (50 mL)
  4. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-2a7aff729eb94143a6240a446c7bd47e
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Linked notes

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